US2664400A - Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same - Google Patents

Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same Download PDF

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US2664400A
US2664400A US110236A US11023649A US2664400A US 2664400 A US2664400 A US 2664400A US 110236 A US110236 A US 110236A US 11023649 A US11023649 A US 11023649A US 2664400 A US2664400 A US 2664400A
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reaction
soyamine
reaction product
acid pyrophosphate
reaction products
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US110236A
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Willard H Woodstock
Thomas M Beck
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Victor Chemical Works
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Victor Chemical Works
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/098—Esters of polyphosphoric acids or anhydrides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/043—Ammonium or amine salts thereof

Definitions

  • This invention relates to reaction products of an octyl acid pyrophosphate and a soyamine and lubricants containing the same.
  • This reaction product when added in small amounts to lubricating oils has been found capable of protecting metal surfaces from rust even under severe conditions of use.
  • soyamine and dioctyl acid pyrophosphate will give excellent protection against rusting of ferrous metals in both ordinary water and sea water, even when the reaction product is present in relatively low concentrations in the lubricant.
  • the soyamine used in preparing the reaction product of this invention may be considered as a mixture of primary aliphatic amines prepared from soybean oil by subjecting the latter to hydrolysis and converting the carboxylater groups of the resulting fatty acids to amino groups.
  • the latter may be accomplished, for example, by neutralizing the acids with ammonia, dehydrating the ammonium carboxylates to form the corresponding nitriles, and finally reducing the nitriles to amines.
  • soyamines generally contain about 85 to 98% of primary aliphatic amines of 16 to 18 or more carbon atoms with about 80% of the amine content being in the form of unsaturated compounds such as octadecenyl and octadecadienyl primary amines. At least 70% of the preferred soyamine consists oi unsaturated aliphatic primary amines having at least 18 carbon atoms in the chain.
  • a typical commercial soyamine known as Armeen SD (Distilled) contained 97% of primary amines 01" which was hexadecyl amine, 35% was octadecenyl amine, and 45% was octadecadienyl amine.
  • soyamines of the above type may be reacted in various proportions with dioctyl acid pyrophosphate to form an oil-soluble reaction product which has utility as a rust inhibitor in lubricants and as intermediates in the production of other organic phosphorus containing products.
  • the reaction is exothermic and it is preferred to control the reaction so as to avoid temperatures which might cause decomposition.
  • a temperature of about 50 to 80 C. is quite satisfactory, though somewhat tures may be employed.
  • Reaction products in gen to phosphorus are less than 1 are not as satwith ratios of 1 to 2.5 moles of soyamine per atom of phosphorus.
  • Efcampl'e 1.'-'-Io 183.5 grams of distilled soyamine (97% primary amine) having an average molecular weightof 296 was slowly added 125 grams of dioctyl acid pyrophosphate while maintaining a temperature of about C. exothermic reaction had ceased the mixture was stirredforapproximately one hour to insure completion of the reaction.
  • the product was quite efiective at 0.025% concentration in solvent-refined lubricating oil, in preventing the corrosion of steel in sea water.
  • Example 3 The procedure of Example 1 was employed to make a reaction product from dioctyl acid pyrophosphate and a crude soyamine containing approximately 85% of primary aliphatic amines about of which were long chain unsaturated aliphatic amines. The proportions employed corresponded to a nitrogen to phosphorus ratio of approximately 1.1 to 1 (or a mol ratio of amine to pyrophosphate of 2.2 to 1). The product was similar to that of Example 1 and substantially as eifective as a corrosion inhibitor in lubricating oils.
  • Example 4Dioctyl acid pyrophosphate was reacted with a soyamine having the approximate composition: 20% hexadecylamine, 50% 9-octadecenylamine, and 30% 9,12-octadecadienylamine to form a clear very viscous, pale amber material with a specific gravity of about 0.95.
  • the reaction product had a molar ratio of nitrogen to phosphorus of about 1.0 and a pH of about 3 5.
  • This product was tested in a solvent-refined lubricating oil for its ability to protect metal surfaces from the rusting action of sea water. The reaction product was added to each of several samples of the same oil with a different concentration in each.
  • reaction products of the first three examples passed the resulting test with but few failures at the 0.025% concentration in the case of Examples 2 and 3. All samples of Examples 1 to 4 passed the rusting test at 0.05 concentration.
  • the preferred dioctyl acid pyrcphosphate is the one having the Z-ethylhexyl isomer as each octyl group.
  • Lubricants conta'ning reaction products of an alkyl acid phosphate and soyamine are disclosed and claimed in our copending application Serial No. 110,237, filed August 13, 1949.
  • reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least 70% of unsaturated aliphatic primary amines each having at least 18 carbon atoms in 4 the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
  • a lubricant for ferrous metals comprising a hydrocarbon oil and a rust-inhibiting quantity of an oil-soluble reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least of unsaturated aliphatic primary amines each having at least 18 carbon atoms in the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.

Description

Patented Dec. 29, 1953 UNITE pc'rs or AN, PYROPHOSPHATE AND so A I E .AND LUBRICANTS CONTAINING THE SAME REACTION PRO ocTiZL non) Willard H. Woodstock, Crete, and Thomas M.
Beck, Homewood,
assignors to Victor Chemical Works, a corporation of Illinois No Drawing. ApplicationAugust 13, 19.49, Serial No. 110,236
Claims. (01. 252- -32 :5)
This invention relates to reaction products of an octyl acid pyrophosphate and a soyamine and lubricants containing the same. This reaction product when added in small amounts to lubricating oils has been found capable of protecting metal surfaces from rust even under severe conditions of use.
An number of oil additives have in the past as rust inhibitors, but been satisfactory for use in lubricating oils where severe corrosion conditions are encountered such as arepresent where the lubricated surfaces come in contact with sea water.
been proposed these have not We have found that the reaction product of.
soyamine and dioctyl acid pyrophosphate will give excellent protection against rusting of ferrous metals in both ordinary water and sea water, even when the reaction product is present in relatively low concentrations in the lubricant. v
The soyamine used in preparing the reaction product of this invention may be considered as a mixture of primary aliphatic amines prepared from soybean oil by subjecting the latter to hydrolysis and converting the carboxylater groups of the resulting fatty acids to amino groups. The latter may be accomplished, for example, by neutralizing the acids with ammonia, dehydrating the ammonium carboxylates to form the corresponding nitriles, and finally reducing the nitriles to amines. Commercially obtainable soyamines generally contain about 85 to 98% of primary aliphatic amines of 16 to 18 or more carbon atoms with about 80% of the amine content being in the form of unsaturated compounds such as octadecenyl and octadecadienyl primary amines. At least 70% of the preferred soyamine consists oi unsaturated aliphatic primary amines having at least 18 carbon atoms in the chain. A typical commercial soyamine known as Armeen SD (Distilled) contained 97% of primary amines 01" which was hexadecyl amine, 35% was octadecenyl amine, and 45% was octadecadienyl amine.
We have found that soyamines of the above type may be reacted in various proportions with dioctyl acid pyrophosphate to form an oil-soluble reaction product which has utility as a rust inhibitor in lubricants and as intermediates in the production of other organic phosphorus containing products. The reaction is exothermic and it is preferred to control the reaction so as to avoid temperatures which might cause decomposition. A temperature of about 50 to 80 C. is quite satisfactory, though somewhat tures may be employed.
higher temperacontaining acids as impurities.
Reaction products in gen to phosphorus are less than 1 are not as satwith ratios of 1 to 2.5 moles of soyamine per atom of phosphorus. 'A reaction product having 'a ratio within "the rangeof 1 to 1.1 "is generally preferred. Suitable reaction products were made in accordance with the following examples,
Efcampl'e 1.'-'-Io 183.5 grams of distilled soyamine (97% primary amine) having an average molecular weightof 296 was slowly added 125 grams of dioctyl acid pyrophosphate while maintaining a temperature of about C. exothermic reaction had ceased the mixture was stirredforapproximately one hour to insure completion of the reaction. was a low melting oil-soluble solid and represents the addition reaction productof 2 moles of soyamine-and 1 mole of dioctyl acid pyrophosphate. The product was quite efiective at 0.025% concentration in solvent-refined lubricating oil, in preventing the corrosion of steel in sea water.
eating grade hydrocarbon oils and was quite efiective as a corrosion inhibitor in such oils at concentrations as low as 0.05%.
Example 3.The procedure of Example 1 was employed to make a reaction product from dioctyl acid pyrophosphate and a crude soyamine containing approximately 85% of primary aliphatic amines about of which were long chain unsaturated aliphatic amines. The proportions employed corresponded to a nitrogen to phosphorus ratio of approximately 1.1 to 1 (or a mol ratio of amine to pyrophosphate of 2.2 to 1). The product was similar to that of Example 1 and substantially as eifective as a corrosion inhibitor in lubricating oils.
Example 4.Dioctyl acid pyrophosphate was reacted with a soyamine having the approximate composition: 20% hexadecylamine, 50% 9-octadecenylamine, and 30% 9,12-octadecadienylamine to form a clear very viscous, pale amber material with a specific gravity of about 0.95. The reaction product had a molar ratio of nitrogen to phosphorus of about 1.0 and a pH of about 3 5. This product was tested in a solvent-refined lubricating oil for its ability to protect metal surfaces from the rusting action of sea water. The reaction product was added to each of several samples of the same oil with a different concentration in each. Each of these samples was subdivided into four test portions and tested according to A. S. T. M. method D-665-42T, but using, in place of the distilled water specified therein a synthetic sea water prepared according to Procedure B of A. S. T. M. method D665'-47T.
All four portions of each of the four oil samples containing respectively 0.025, 0.05, 0.1 and 0.2% by weight of the reaction product passed the test. A sample of the same oil containing no additive failed to pass the test.
When tested in a manner similar to the above, the reaction products of the first three examples passed the resulting test with but few failures at the 0.025% concentration in the case of Examples 2 and 3. All samples of Examples 1 to 4 passed the rusting test at 0.05 concentration.
When using soyamine as the sole additive to the lubricating oil, the resulting tests failed at all of the concentrations mentioned above.
The preferred dioctyl acid pyrcphosphate is the one having the Z-ethylhexyl isomer as each octyl group.
Lubricants conta'ning reaction products of an alkyl acid phosphate and soyamine are disclosed and claimed in our copending application Serial No. 110,237, filed August 13, 1949.
Having disclosed our invention in considerable detail, it is our intention that the invention be not limited by any of the details of description unless otherwise specified, but rather be construed broadly within its spirit and scope as set out in the accompanying claims.
We claim:
1. The reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least 70% of unsaturated aliphatic primary amines each having at least 18 carbon atoms in 4 the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
2. The reaction product of claim 1 wherein said ester is the substantially pure dioctyl acid pyrophosphate.
3. The reaction product of claim 1 wherein the proportions are approximately one mole of amine per one atom of phosphorus.
4. A lubricant for ferrous metals comprising a hydrocarbon oil and a rust-inhibiting quantity of an oil-soluble reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least of unsaturated aliphatic primary amines each having at least 18 carbon atoms in the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
5. The lubricant of claim 4 wherein the ester of said reaction product is the substantially pure dioctyl acid pyrophosphate.
WILLARD H. WOCDSTOCK. THOMAS M. BECK.
References Cited in the file of this patent OTHER REFERENCES Gerrard, J. Chem. Soc. (London), pages 1464 to 1469 (1940). (Copy available in Scientific Library.)

Claims (1)

  1. 4. A LUBRICANT FOR FERROUS METALS COMPRISING OF HYDROCARBON OIL AND A RUST-INHIBITING QUANTITY OF AN OIL-SOLUBLE REACTION PRODUCT PREPARED BY REACTING A DIOCTYL ACID ESTER OF PYROPHOSPHORIC ACID WITH 1 TO 2.5 MOLES, PER ATOM OF PHOSPHORUS IN THE ESTER, OF AN AMINE COMPOSITION CONTAINING AT LEAST 70% OF UNSATURATED ALIPHATIC PRIMARY AMINES EACH HAVING AT LEAST 18 CARBON ATOMS IN THE MOLECULE UNTIL THE REACTION IS SUBSTANTIALLY COMPLETED, THE REACTION BEING CARRIED OUT AT A TEMPERATURE BELOW THAT AT WHICH SUBSTANTIAL DECOMPOSITION OF THE REACTION PRODUCT OCCURS.
US110236A 1949-08-13 1949-08-13 Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same Expired - Lifetime US2664400A (en)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2841126A (en) * 1955-05-09 1958-07-01 Gulf Oil Corp Marine diesel fuel compositions and methods of operating marine diesel engines
US2848414A (en) * 1955-11-23 1958-08-19 Universal Oil Prod Co Corrosion inhibitor
US2863904A (en) * 1955-05-09 1958-12-09 Gulf Oil Corp Amine salts of di oxo-octyl orthophosphates
US2961408A (en) * 1957-06-14 1960-11-22 Shell Oil Co Power transmission mineral oil base fluids
US3000820A (en) * 1959-04-15 1961-09-19 Standard Oil Co Thixotropic oleaginous compositions containing the reaction product of an abietyl amine and an organic phosphate
US3051655A (en) * 1957-11-01 1962-08-28 Quaker Chemical Products Corp Metalworking lubricant
US3150039A (en) * 1960-11-16 1964-09-22 Union Carbide Corp Insecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same
US3504055A (en) * 1967-10-06 1970-03-31 Mobil Oil Corp Neutral primary tertiaralkyl amine salts of tripolyphosphoric acid and phosphoric acid alkyl esters
US3652242A (en) * 1970-02-02 1972-03-28 Mobil Oil Corp Liquid hydrocarbon fuels containing alkylamine salts
WO2018200664A1 (en) * 2017-04-27 2018-11-01 The Lubrizol Corporation Method of lubricating a mechanical device with high pyrophosphate level lubricant
WO2019204141A1 (en) * 2018-04-18 2019-10-24 The Lubrizol Corporation Lubricant with high pyrophosphate level
US11352582B2 (en) 2015-11-06 2022-06-07 The Lubrizol Corporation Lubricant with high pyrophosphate level
US11384308B2 (en) 2016-07-20 2022-07-12 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2005619A (en) * 1934-11-10 1935-06-18 Du Pont Esters of acids of phosphorus
US2080299A (en) * 1935-04-12 1937-05-11 Du Pont Inhibiting corrosion of metals
US2285854A (en) * 1934-02-23 1942-06-09 Du Pont Lubrication
US2371854A (en) * 1943-09-27 1945-03-20 Gulf Oil Corp Mineral oil composition
US2371655A (en) * 1941-12-06 1945-03-20 Gulf Oil Corp Lubricant compositions
US2397381A (en) * 1943-03-19 1946-03-26 Gulf Oil Corp Mineral oil compositions and methods of suppressing foaming in oils
US2400611A (en) * 1945-03-19 1946-05-21 Gulf Oil Corp Turbine oils
US2413852A (en) * 1944-08-30 1947-01-07 Atlantie Refining Company Rust-inhibiting lubricant

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2285854A (en) * 1934-02-23 1942-06-09 Du Pont Lubrication
US2005619A (en) * 1934-11-10 1935-06-18 Du Pont Esters of acids of phosphorus
US2080299A (en) * 1935-04-12 1937-05-11 Du Pont Inhibiting corrosion of metals
US2371655A (en) * 1941-12-06 1945-03-20 Gulf Oil Corp Lubricant compositions
US2397381A (en) * 1943-03-19 1946-03-26 Gulf Oil Corp Mineral oil compositions and methods of suppressing foaming in oils
US2371854A (en) * 1943-09-27 1945-03-20 Gulf Oil Corp Mineral oil composition
US2413852A (en) * 1944-08-30 1947-01-07 Atlantie Refining Company Rust-inhibiting lubricant
US2400611A (en) * 1945-03-19 1946-05-21 Gulf Oil Corp Turbine oils

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2841126A (en) * 1955-05-09 1958-07-01 Gulf Oil Corp Marine diesel fuel compositions and methods of operating marine diesel engines
US2863904A (en) * 1955-05-09 1958-12-09 Gulf Oil Corp Amine salts of di oxo-octyl orthophosphates
US2848414A (en) * 1955-11-23 1958-08-19 Universal Oil Prod Co Corrosion inhibitor
US2961408A (en) * 1957-06-14 1960-11-22 Shell Oil Co Power transmission mineral oil base fluids
US3051655A (en) * 1957-11-01 1962-08-28 Quaker Chemical Products Corp Metalworking lubricant
US3000820A (en) * 1959-04-15 1961-09-19 Standard Oil Co Thixotropic oleaginous compositions containing the reaction product of an abietyl amine and an organic phosphate
US3150039A (en) * 1960-11-16 1964-09-22 Union Carbide Corp Insecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same
US3504055A (en) * 1967-10-06 1970-03-31 Mobil Oil Corp Neutral primary tertiaralkyl amine salts of tripolyphosphoric acid and phosphoric acid alkyl esters
US3652242A (en) * 1970-02-02 1972-03-28 Mobil Oil Corp Liquid hydrocarbon fuels containing alkylamine salts
US11352582B2 (en) 2015-11-06 2022-06-07 The Lubrizol Corporation Lubricant with high pyrophosphate level
US11384308B2 (en) 2016-07-20 2022-07-12 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants
WO2018200664A1 (en) * 2017-04-27 2018-11-01 The Lubrizol Corporation Method of lubricating a mechanical device with high pyrophosphate level lubricant
CN110573599A (en) * 2017-04-27 2019-12-13 路博润公司 Method for lubricating a mechanical device with a lubricant having a high pyrophosphate content
US11180710B2 (en) 2017-04-27 2021-11-23 The Lubrizol Corporation Method of lubricating a mechanical device with high pyrophosphate level lubricant
CN110573599B (en) * 2017-04-27 2022-04-26 路博润公司 Method for lubricating a mechanical device with a lubricant having a high pyrophosphate content
WO2019204141A1 (en) * 2018-04-18 2019-10-24 The Lubrizol Corporation Lubricant with high pyrophosphate level
CN112055743A (en) * 2018-04-18 2020-12-08 路博润公司 Lubricant with high pyrophosphate content
CN112055743B (en) * 2018-04-18 2022-11-04 路博润公司 Lubricant with high pyrophosphate content

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